15 Best Places to Shop in Massachusetts, USA

A special place, Brewster Book Store is filled to the rafters with books by local and international authors, with an extensive fiction selection and kids' section. Author signings and children's story times and craft sessions take place year-round.

Shops don't get more adorable than this downtown candy store with the bright pink awning, winning sweet-toothed fans since 1955 for their slow-cooked, small-batch confections. Their version of a clambake is a too-cute assortment of chocolate sea creatures on a bed of chocolate rocks. Sea salt caramels, made with local sea salt, are a favorite, and they stay open year-round.

Jam-packed with toys, games, and more bizarre novelty items than you could possibly imagine, this store benefits from the enthusiasm of owners Ken and Michele Gietz. Grab an offbeat gift for a friend (and some of the interesting candies for yourself).

Step back in time with a visit to Alley's General Store, a local landmark and gathering place since 1858, and the island's oldest retail business. Stock includes everything from groceries to gourmet cheeses, and toys for all ages, from stuffed animals for the kids to housewares for adults. Alley's is a treasure trove of the playful and practical items that define a country store. The coffee bar sells some of the best brew in town, and they offer a great selection of snacks for a beach day.

Shipping-container-like buildings line a busy stretch of Seaport Boulevard, each housing pop-up shops by local entrepreneurs looking to get their retail ventures off the ground. Container residents change with the season, but may include sweets shops, consignment, jewelry, men's fashions, parfumiers, and more.

Need a unique gift for a tot under the age of three years old? This small store stocks classic books and quality toys you definitely won't find at big chain stores. Check out the unparalleled collection of LEGO, Playmobil, and Calico Critters.

More than 100 makers and artisans come together during the winter holidays for this open-air market. Visitors can sample foods from local food trucks and dessert vendors, or get a warm or alcoholic beverage at four bars. Stop for a selfie, have a hot chocolate, and enjoy the twinkling string lights.

Fudge, chocolate, caramel corn, ice cream, and taffy are some of the sweet reasons to visit this family-run shop, open all year (no ice cream in winter). The front of the store is devoted to display cases of fine chocolates and old-fashioned "penny" candy. Some of the chocolates (caramels, fudge, filled chocolates) and all of the saltwater taffy and ice cream are made in-house. In the back are gifts galore: sea glass ornaments, Cape-made soap, lobster-printed onesies, and other items with a beach vacation theme. Take a selfie out front with Bert, the big stuffed bear, propped on a bench. 

Looking for a souvenir to take home? Maybe something you've made? Book an appointment at Little Words Project at the beading table to make your own bracelet, or browse the already made pieces. Each beaded bracelet includes a short message—it's the project's mission to empower people with words of affirmation—and a portion of the proceeds goes to different nonprofit organizations. 

Did you pack wrong for Boston's unpredictable weather? This multi-floor fast-fashion U.K.-based department store is just the place to supplement your wardrobe without putting a dent in your spending money. Clothing (for men, women, and kids), cosmetics, luggage, home goods, shoes, and more are available.

As the name suggests, Rainy Day carries gifts and amusements perfect for one of the island's gloomy afternoons when you just need a warm, dry diversion. You'll find toys, crafts, books, puzzles, island-made soap and other products, island-inspired home goods, and more.

You'll feel like a kid in a candy shop, no matter what your age is, in this store packed with hard-to-find sweets that you haven't seen since childhood. Owner Robin Helfand searches out and buys up vintage candy and keeps a stock of jelly beans in just about every flavor imaginable.

Local businesses, including those owned by women and minorities, make up the vendors at this annual outdoor vendor market. Housewares and pottery, jewelry and clothing, artwork, cosmetics, and pet goods are among the unique wares to browse. Bring the kids because this market is quite family friendly with a DJ and games, Children's Museum programming, and lots of food.

This too-cute—and a bit bohemian—mom-and-kid clothing store features looks from fairly expensive, small brands, and there's no question as to its place in Beacon Hill society. This is where the neighborhood women come to buy frocks that aren't made to be worn to the office. There's also a nice selection of toys and kid gift items, including stuffed animals and sensory jars.

Well-worn wooden floors and old-time music provide an authentic feel that pairs well with the country-store staples for sale here: toys, maple goodies, jams, and an abundance of candy.

Don't confuse Williams and Sons with the sparse "general store" down the street.